


Sleeping with the wrong Winchester.

by fictionalabyss



Category: Supernatural
Genre: F/M, Oral Sex, Penis Size, Vaginal Sex
Language: English
Status: Completed
Published: 2017-10-09
Updated: 2017-10-09
Packaged: 2020-01-12 22:03:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,032
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18455492
Author URL: https://archiveofourown.org/users/fictionalabyss/pseuds/fictionalabyss
Summary: Dean's self conscious about his size after a friend of yours makes him feel bad.You convince him to show you what he can do with it.





	Sleeping with the wrong Winchester.

**Author's Note:**

> I just wanted one fic where a Winchester didn't have a dick the size of my damn forearm, so I wrote one.

Dean _fucking_ Winchester. Gods gift to women, if you listen to the bullshit he spews. And it is that. Bullshit. Or so you thought, at first.

You had met the Winchester boys when your suddenly jealous and abusive boyfriend turned out to be a werewolf. And something had happened between you and Sam. Apparently, that happens to him often. He swoops in to save a girl, fucks her, and sometimes she ends up dead. Or turns out to be a monster. You were lucky to be neither. Thanks to Dean.

He shot the bastard in the heart with a silver bullet while you and Sam slept. His body dropping on top of you like ton of bricks, scaring the shit out of you. Dean had just winked at you and walked out.

They had left town soon after, and you thought you’d never seen them again. But your eyes were open to the world that was. The monsters we tell our children  aren’t real, when in reality they lurk around every corner. And the only thing between you and them, were hunters.

You were no hunter. Far from it. But, you were pretty good at retaining random information that seemed useless to most people. Research it is.  You’d travel around, offering help to hunters who needed someone doing quick research. Mostly hunters working alone.

It’s what brought you to the city you were currently in. You had been there for a few weeks. Something small had popped up, but it was enough to peak your curiosity. You had some old, school friends who happened to be living there, and they were glad to have you visit. Two more deaths happened before you saw Dean Winchester walk into the bar. You raised an eyebrow when he walked right past you. But smiled when Sam came in and spotted you right away.

“Y/N? What the hell are you doing here?” he smiled. He sat across from you. You slid your phone over to him as Dean looked back at Sam confused as to why Sam hadn’t joined him at his table. Sam’s smile faded when he saw what you had been looking at. “You’re a hunter now? Please tell me you’re not.”

You smiled and shook your head at how worried he was. “No, not a hunter. Not really any ways.. I don’t go out ‘into the field’.  I offer research services. Mostly hunters working alone, helping them get the job done quicker. I’ve been here for weeks waiting for a hunter to come. I never thought it would be _you two_.”

He waved over to Dean to join you. “You’ve been here for _weeks_ on this? What do you know?” Dean sat at the chair between you and Sam.

You chuckled “Everything there is to know. I have it all.”

Sam stared at you wide eyed. “ _Everything_ , everything?”

You nodded. “Got everything I could get my hands on as it happened. Statements, Reports, Video, Pictures, Results.. Everything Sam. I even combed over everything and found what it is. I just needed a hunter to find where, and kill it.”

Sam scoffed. “Shit. I think she all but did our job for us, Dean. What the hell are we going to do.”

You smiled. “Follow me for starters. I’ll give you what I have. Then once it’s dead, I’ll introduce Dean here to a few friends we’ll get hammered and celebrate a job well done.”

Dean smiled his typical cocky smile, but he protested introducing him to some friends. Swearing he preferred his methods. You couldn’t figure out why he was refusing, but sighed and nodded.

  
  


Once you got them back to the small two bedroom apartment you were staying in, they were surprised that you really did have everything. You offered to let them stay with you, instead of wasting their money on a motel. This place wasn’t much better, but it was already paid for. Sam accepted, and Dean figured it was just to get in your pants again.

By the next night, the monster was dead, and you had ’ _accidentally_ ’ bumped into some friends at the bar as you celebrated with the boys. Dean wasn’t please, but you couldn’t figure out why. Women fawned over him constantly, and your friends were no exception. A few extra drinks his way, and he eventually left with one of them.

  
  


You woke up late the next morning, half on top of Sam in your bed. You reached over for your phone to see what time it was, and saw a message from your friend.

> I’m never letting you set me up again.

Confused you got out of bed pulling on clothes. You check the other bedroom but found it empty. “What the fuck happened?” You tried to call Dean but got no answer. Sighing, you left Sam a quick note saying you were stepping out and went on the hunt for Dean.

  
  


You weren’t surprised to find him in the bar you had been in last night. “Dean what’s going on.”

“Nothing, sweetheart. Nothing at all.”

“Alright.” You motioned to the bartender ordered six shots.

“What are you doing?”

“If I’m going to figure out what’s eating you, I need to get in your head space. And I don’t drink alone.” You handed him 3 of the shots. “ _Drink_ Winchester.”

You kept the shots coming. Instead of finding out what was wrong with Dean, you both got hammered and started having a blast. After a while you got serious. “Come Deaner, talk to me. I figured you’d be in a good mood today.” He shrugged. “Is the great Dean Winchester, **Gods fucking gift to women** , tired of the one night stands?”

He downed another shot. “Maybe.”

“Then stop having them Dean. Let a girl stay the night once in a while. Come on.” He sighed. “Come on. Come with me, I’m tired of your sulking.”

You grabbed his arm and yanked him off the stool. He almost fell, which would have been bad, because you could barely walk. You both all but carried each other as you walked out and down the street. You guiding him by either bumping your hip against him, or tugging him. “Where are we going?” he asked after a while.

“There.” you motioned towards the motel  across the street.

“What? Why!”

“To cheer you up. Why else?” You dragged him across the street and left him outside as you went in and got a room.

“No really.. we aren’t.”

“We are Dean. We are. 1- Apparently my friend was fucking horrible in the sack because you are _miserable_ after a lay. 2- I’m already horny. 3- Let’s be honest, Dean. I’ve been curious.” You smirked at him.

He tried to protest but you walked away and went into the room. When he didn’t follow, you took off your bra and tossed it out into the parking lot.

He groaned softly and followed you. Stopping to grab your bra before going in. “Don’t do this. Come on.. Didn’t you have fun with Sammy last night? Go fuck him again.”

You stopped and stared at him, your shirt was already on the floor, your jean shorts undone. “What is it Dean. Is it _me_? Am I not attractive enough?” you looked almost sad. He shook his head. “Is it because I’ve fucked your brother? Is that a deal breaker?” He sighed. You reached out and pulled him closer. “Come on, Dean. What’s wrong.”

“I..” He bit his lip then started again. “It’s not you, it’s me. I don’t chose to have one night stands.. they just.. happen.”

“So you’ve been with shitty women, Dean. Come on.” You pulled off his shirt. “I’ll treat you good.” you smiled.

He pulled away when you started to undo his jeans. “Please don’t.”

You pulled him in for a deep kiss. “Just let go Dean. Give me 15 minutes at least. Please.” You kissed him again and his jeans fell to the floor. He tried to pull away again. “5 minutes then.” he groaned when you put his hands on your ass and kissed him again pressing yourself up against him. “Just 5 minutes Dean. Then you can walk out if you want.”

He pushed your shorts down along with your panties. You smiled kicking them aside. When his fingers went to work, he had you gasping in no time. If you were a lesser woman, you would have let him do his thing and forgotten what you wanted to do. But your hands when to his boxer briefs and started pushing them down. He grabbed your wrists in a bruising grip to stop them. “All or nothing, Dean.” Your eyes met his. He was silently pleading with you. “I want this. I want _you_. All of you.” he slowly let go and you pushed them down.

When your eyes moved down his body, a soft smile graced your lips when you looked at his erection.  He groaned. “Let me guess, you expected more right.” He started to pull his boxer briefs back up but you stopped him.

“Is _that_ what this is about? Did she say that to you last night?” The look on his face gave you the answer. “I’ll fucking kill her.” He raised an eyebrow at you. “Why is this bothering you so bad Dean.. You get women all the time.”

He sighed moving away from you and sitting on the bed. “Look at me. Model good looks, of course I get women all the time. But beyond that..” he shrugged. “Some take one look, expected more and walk out. Others are willing to see what I can do. No one’s ever been an asshole about it though.. until…”

“Until my _so called friend_?”

“I saw her message you. She said that’s probably why you were fucking my brother and not me. Betting he has a huge dick, while I have the smallest one she’s seen.”

You groaned. “Yeah, you walked out with the wrong friend. She’s obsessed with porn star big.”

“Isn’t everyone?”

“No, Dean. Not everyone. Not _me_.”

“Don’t just humour me. You’ve been with _Sam_. What’s this compared to him?”

You stood right in front of him and cupped his face. “Do you know how to use what you’ve got?” He nodded. “Show me. Big dicks **hurt** , Dean, and I’ve had smaller. Make me scream your name. I have a feeling you can do that in a minute.”

He smiled. “You really want to do this?”

You sat in his lap kissing him deeply before pushing him back on the bed.  "Give me your best shot, Winchester.“

He groaned and rolled you over, kicking his boxer briefs all the way off. The look on his face was glorious. His confidence was back. He had a beautiful woman who wanted him even though she’d had bigger.

And man did Dean know how to work. Your first orgasm ripped through you with just his fingers on your clit. The second was with his tongue alone. The third, was while his licked your clit and fingered your pussy. By the time he moved over you and lined himself up, you were so sensitive. You screamed out with the first thrust as his pelvis slammed against your swollen and sensitive clit. And that’s how he worked his magic.

He knew all the angles to make the most of it, so it wasn’t all stimulation. Even though he wasn’t as big as his brother, he was hitting all the right spots.

“ **Dean!** Oh, fuck, Dean… I’m close… _Jesus_ …” Your nails were digging into his  biceps, your ankles on his shoulders, his weight on his hands holding himself up, so your hips were tilted forward. “ **Fuck, Dean! For the love of god, please cum with me**.”

He took one leg off his shoulder, and his thumb rubbed your clit. You screamed out and clamped down, the most powerful orgasm you ever had ripped through your body. “Fuck, baby!” Dean groaned, as he pulsed and filled you.

When you were both laying in the bed panting, you started to laugh.

“What?” He looked at you worried.

“I’ve been fucking the wrong Winchester. That’s what.”


End file.
